1.02011-09-21 01:04:42 UTC2019-11-26 03:21:22 UTCFDB026010PC(24:1(15Z)/P-18:1(9Z))PC(24:1(15Z)/P-18:1(9Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:1(15Z)/P-18:1(9Z)), in particular, consists of one chain of nervonic acid at the C-1 position and one chain of plasmalogen 18:1n9 at the C-2 position. The nervonic acid moiety is derived from fish oils, while the plasmalogen 18:1n9 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.
While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. [HMDB]1-Nervonoyl-2-(1-enyl-oleoyl)-sn-glycero-3-ocholine1-nervonoyl-2-(1-enyl-oleoyl)-sn-glycero-3-phosphocholineC50H96NO7P854.2735853.692440943trimethyl(2-{[2-(octadeca-1,9-dien-1-yloxy)-3-(tetracos-15-enoyloxy)propyl phosphonato]oxy}ethyl)azaniumtrimethyl(2-{[2-(octadeca-1,9-dien-1-yloxy)-3-(tetracos-15-enoyloxy)propyl phosphonato]oxy}ethyl)azaniumCCCCCCCCC=CCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC=CCCCCCCC=CCCCCCCCCInChI=1S/C50H96NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-28-29-31-33-35-37-39-41-43-50(52)56-47-49(48-58-59(53,54)57-46-44-51(3,4)5)55-45-42-40-38-36-34-32-30-23-21-19-17-15-13-11-9-7-2/h20-23,42,45,49H,6-19,24-41,43-44,46-48H2,1-5H3ZLQCRABYIDJNLT-UHFFFAOYSA-N belongs to the class of organic compounds known as 1-acyl,2-(1z-alkenyl)-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O1-position, and one 1Z-alkenyl chain attached through an ether linkage at the O2-position.1-acyl,2-(1Z-alkenyl)-glycerophosphocholinesOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphocholinesAliphatic acyclic compoundsAminesCarbonyl compoundsCarboxylic acid estersDialkyl phosphatesFatty acid estersGlycerol vinyl ethersHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOrganic saltsOrganopnictogen compoundsPhosphocholinesTetraalkylammonium salts1-acyl,2-(1z-alkenyl)-glycerophosphocholineAliphatic acyclic compoundAlkyl phosphateAmineCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterDialkyl phosphateFatty acid esterFatty acylGlycerol vinyl etherHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic saltOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhosphocholinePhosphoric acid esterQuaternary ammonium saltTetraalkylammonium saltSolidlogp7.00logs-7.60solubility2.29e-05 g/llogp12.23pka_strongest_acidic1.86pka_strongest_basic-4.8iupactrimethyl(2-{[2-(octadeca-1,9-dien-1-yloxy)-3-(tetracos-15-enoyloxy)propyl phosphonato]oxy}ethyl)azaniumaverage_mass854.2735mono_mass853.692440943smilesCCCCCCCCC=CCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC=CCCCCCCC=CCCCCCCCCformulaC50H96NO7PinchiInChI=1S/C50H96NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-28-29-31-33-35-37-39-41-43-50(52)56-47-49(48-58-59(53,54)57-46-44-51(3,4)5)55-45-42-40-38-36-34-32-30-23-21-19-17-15-13-11-9-7-2/h20-23,42,45,49H,6-19,24-41,43-44,46-48H2,1-5H3inchikeyZLQCRABYIDJNLT-UHFFFAOYSA-Npolar_surface_area94.12refractivity264.45polarizability109.98rotatable_bond_count47acceptor_count4donor_count0physiological_charge0formal_charge0HMDB08820AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930Cow milk, pasteurized, vitamin A + D added, 0% fatType 2specificCow milk, pasteurized, vitamin A + D added, 1% fatType 2specificCow milk, pasteurized, vitamin A + D added, 2% fatType 2specificCow milk, pasteurized, vitamin D added, 3.25% fatType 2specificDeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa98232-acylglycerol O-acyltransferase 2Q3SYC2MOGAT2Acyl-protein thioesterase 1O75608LYPLA1Acyl-protein thioesterase 2O95372LYPLA2Choline kinase alphaP35790CHKACholine-phosphate cytidylyltransferase AP49585PCYT1ACholine-phosphate cytidylyltransferase BQ9Y5K3PCYT1BEosinophil lysophospholipaseQ05315CLCLecithin retinol acyltransferaseO95237LRATLysophosphatidylcholine acyltransferase 2Q7L5N7LPCAT2Lysophospholipid acyltransferase 5Q6P1A2LPCAT3Neuropathy target esteraseQ8IY17PNPLA6Phosphatidylcholine-sterol acyltransferaseP04180LCATPhosphatidylcholine:ceramide cholinephosphotransferase 1Q86VZ5SGMS1Phosphatidylcholine:ceramide cholinephosphotransferase 2Q8NHU3SGMS2Phosphatidylethanolamine-binding protein 1P30086PEBP1Phosphatidylethanolamine-binding protein 4Q96S96PEBP4Phosphatidylserine synthase 1P48651PTDSS1Phospholipase D2O14939PLD2Phospholipase D3Q8IV08PLD3Phospholipase D4Q96BZ4PLD4Phospholipase D6Q8N2A8PLD6